Hydrochloric Acid → N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide

Participants

Reaction Steps

To a suspension of 450 mg of N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide and 476 mg of potassium carbonate in 5 ml of N,N-dimethylformamide, 313 mg of 2-iodopropane was added, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was mixed with 20 ml of water and extracted with ethyl acetate (25 ml×2), the resulting organic layers were combined, washed with water (20 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent to obtain 121 mg of a colorless resinous substance. The resinous substance was dissolved in 10 ml of ethanol, the solution was mixed with 1 ml of a 1,4-dioxane solution (4 mol/L) of hydrogen chloride and stirred at 70° C. for 5 hours, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent to obtain 99 mg of the desired product as a colorless resinous substance (E/Z=50/50).

Provenance & Evidence